
Waterfront holiday rentals near Siesta Beach
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals near Siesta Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

NO Stairs, Siesta beachfront. Walk to the village!
Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

Beachwalk Townhouse with view of Gulf of Mexico
Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

Island Time: Open July 7 - 10!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

The Palm Bay Club on Siesta key Beach
Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

Palm Bay Club! Resort Living on Siesta Key!
Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Siesta Key Quaint Beach House
This home, built in the 1950’s, has old Florida highlights including cypress wood walls and terrazzo floors located in a peaceful neighborhood. It is all on one level and sleeps 4 adults with a private patio including a gas grill. It’s only a 5 minute walk to Siesta Key beach and includes a beach cart, chairs, umbrella, towels and a cooler. Only a 10 minute walk or 2 minute ride to the village with shops, restaurants, music and nightlife.

Stylish & Bright: Steps to Beach ~ Pool ~ Hot Tub!
Escape to this colorful 2BR beachfront duplex in the heart of Siesta Key, just steps from the beach, restaurants, and local attractions. Enjoy modern comforts, a private cabana with a hot tub, and access to a shared pool—perfect for couples, families, and beach lovers. ☀ Shared pool ☀ Steps to the beach ☀ Pet-friendly ☀ BBQ area ☀ Private hot tub ☀ Pets allowed ☀ Wifi & Free parking Your perfect seaside escape awaits!

On the Beach; Siesta Key SunBum Studio
Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs.

Siesta Sunsets Suite
Siesta Sunset Suite....experience Private Beach access to Americas #1 Beach and #1 Sunset! It's truly a one of a kind experience, as the beach is just steps outside your door! Also your choice, move from the sea and sand life to the Siesta by the pool. We do require a 2 night minimum stay. The free Siesta Key trolly stop is nearby, so don't miss the restaurants, terrific shopping, and Beachy nightlife.

Beach, Village, Dock & Private Pool! One-of-a-kind
Rad’s Cozy Cottage – Siesta Key Private Home. Enjoy a heated saltwater pool, canal-front dock, and putting green at this one-of-a-kind tropical getaway. Steps from Siesta Village (shops, restaurants, nightlife) and the powdery-white sands of Siesta Key Beach. Fully updated 2BR/1.5BA cottage with modern kitchen, AC, Wi-Fi, and washer/dryer. Sleeps 6 (king + 2 twins + sofa). Book your island paradise!

Siesta Key Oasis with Gulf Views
Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 5th floor unit has an extra large lanai that provides some of the best Gulf views on Siesta Key! 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year!
Popular amenities for waterfront rentals near Siesta Beach
Waterfront apartment rentals

Newly Remodeled Beachfront Studio - On the sand!

Sweet Retreat at Shorewalk!

Pass a grille Gulf Way Beachfront Parking WiFi 13

Longboat Key-OCEAN FRONT- on the beach

Modern Garden Condo w/ Heated Pool | 1BR

Serenity on the Manatee

Siesta Premier Location - The 'Calm of Siesta'

Siesta Key Condo. Sit by the water !
Waterfront house rentals

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

Luxury 3B/3B waterfront home w/ pool + boat access

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

Summer House longboat key

Luxury Canal-Front Home + Heated Pool Near Beach

Silent G Siesta Key Private Bungalow by the Beach

Mid-Century Modern, Pool, Mins to Siesta Key Beach

Rustic Sands - 650
Waterfront apartment rentals

Siesta Key For Me @ The Palm Bay Club

Sarasota Surf & Racquet Club Siesta Key Condo

KING Bed + Anna Maria Island Beaches + Beach Gear!

Penthouse 20ft to Beach Access, 500ft from Village

Sunset and beach view from your balcony Unit 403

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

Siesta Key Beach (OHAB) Townhouse #1 beach

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool
Other waterfront holiday rentals

Siesta Key Beach front 2 bedroom condo w/ parking

Anchorage Resort 2 bedroom Condo with Beach Access

Luxury Waterfront Home in Sarasota w/ Pool & Dock

Serene Lakehouse Condo on Siesta Key Beach

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!

Waterfront Retreat | Heated Pool & Boat Dock

Beach Front Haven

True Island Living House/beach/water views
Quick stats about waterfront rentals near Siesta Beach

Total holiday rentals
Explore 480 holiday rentals in Siesta Beach

Nightly prices starting at
Siesta Beach holiday rentals start at €105 per night before taxes and fees

Verified guest reviews
Over 13,170 verified reviews to help you choose

Family-friendly holiday rentals
380 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
440 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wifi availability
480 of Siesta Beach holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Siesta Beach rentals

4.8 Average rating
Siesta Beach stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Pet-friendly rentals Siesta Beach
- Rentals with a firepit Siesta Beach
- Rentals with pools Siesta Beach
- Townhouse rentals Siesta Beach
- Beach house rentals Siesta Beach
- Luxury rentals Siesta Beach
- Rentals with breakfast Siesta Beach
- Rentals with a washing machine and dryer Siesta Beach
- Cottage rentals Siesta Beach
- Rentals with a hot tub Siesta Beach
- Rentals with a patio Siesta Beach
- Rentals with a fireplace Siesta Beach
- Villa rentals Siesta Beach
- Rentals with a kayak Siesta Beach
- Apartment rentals Siesta Beach
- Rentals with an EV charger Siesta Beach
- Beachfront rentals Siesta Beach
- Rentals with outdoor seating Siesta Beach
- Flat rentals Siesta Beach
- Rentals with beach access Siesta Beach
- House rentals Siesta Beach
- Rentals with lake access Siesta Beach
- Family-friendly rentals Siesta Beach
- Fitness-friendly rentals Siesta Beach
- Waterfront rentals Sarasota County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- Raymond James Stadium
- Anna Maria Island Beach
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
- Vinoy Park
- Tampa Convention Center
- Manasota Key Beach
- Crescent Beach
- John's Pass
- Fort De Soto Park
- Tropicana Field
- Englewood Beach
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Jannus Live
- Img Academy
- Cortez Beach
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park





